Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][O:11][C:12](=[O:16])[C:13]#[C:14][CH3:15].N12CCCN=C1CCCCC2>O1CCCC1>[CH3:10][O:11][C:12](=[O:16])/[CH:13]=[C:14](/[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)\[CH3:15]Participants
Procedure
To a stirred mixture of 3-hydroxy-benzonitrile (3.30 g, 0.028 mol) and methyl-2-butynoate (5.40 g, 0.055 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.20 g, 0.028 mol) slowly. After addition was complete the mixture was stirred at reflux for 6 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue dried under high vacuum which afforded (E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester as an oil (4.60 g, 76%) and used without further purification.
Workup
- additionAfter addition
- temperatureat reflux for 6 h
- customwas removed in vacuo
- additionthe residue was diluted in diethyl ether
- washwashed first with 1N aqueous hydrochloric acid
- dry with material10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate
- filtrationThe mixture was filtered
- customevaporated
- customthe residue dried under high vacuum which
Sources & evidence
- ORD record
- ord-fb3e6c940794475996d3ab2a68d25e21
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Linked notes
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